David Shippey
863.521.4517

Siesta Isles Real Estate

Market Snapshot of Listings in Siesta Isles - Sarasota, FL 34242
The current prices for all Real Estate Listings in Siesta Isles - Sarasota, FL are reflected in the the table below.
Averages based on current search criteria as of 07/23/2025 6:32 PM
Class Total Number Price Beds Baths Age
Vacant Land2$925,000---
Rental4$6,1242.5258.8
Residential11$1,683,7893.12.755.6
Displaying results 1-10 of 17
69 Photos 5569 Cape Leyte Drive Sarasota, FL 34242

5569 Cape Leyte Drive
Sarasota, FL 34242
Siesta Isles
Residential

MLS# A4656098 / Active
3 Beds, 4.00 Total Baths, 4 Full Bath, 3654 Sqft
Area: 34242 - Sarasota/crescent Beach/siesta Key, Subdivision: Siesta Isles

LOCATION, LOCATION, LOCATION !!!Live like a Lottery Winner on the Crystal Sands & Aqua Waters of Siesta Key. Literally, You can walk one block to b... 

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$4,999,777
Provided courtesy of MICHAEL SAUNDERS & COMPANY
25 Photos 951 Contento St. Siesta Key, FL 34242

951 Contento St.
Siesta Key, FL 34242
Siesta Isles
Residential

MLS# A4639209 / Active
3 Beds, 4.00 Total Baths, 4 Full Bath, 2882 Sqft
Area: 34242 - Sarasota/crescent Beach/siesta Key, Subdivision: Siesta Isles

Under Construction: Nestled in one of Siesta Keys best-kept secrets, The Coastal Haven is tucked away in the peaceful privacy of a relaxing cul-de-... 

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$2,299,000
Provided courtesy of COLDWELL BANKER SARASOTA CENT.
97 Photos 1038 Contento Street Sarasota, FL 34242

1038 Contento Street
Sarasota, FL 34242
Siesta Isles
Residential

MLS# A4650938 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2217 Sqft
Area: 34242 - Sarasota/crescent Beach/siesta Key, Subdivision: Siesta Isles

Siesta Key Canal Front Home with 175 of sea wall on the Grand Canal in the desirable and quaint neighborhood of Siesta Isles. Ride your bike to the... 

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$1,725,000
Provided courtesy of SARASELLSSARASOTA.COM
81 Photos 5581 Shadow Lawn Drive Sarasota, FL 34242

5581 Shadow Lawn Drive
Sarasota, FL 34242
Siesta Isles
Residential

MLS# A4653589 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2120 Sqft
Area: 34242 - Sarasota/crescent Beach/siesta Key, Subdivision: Siesta Isles

Your Siesta Key dream starts right here! This spectacular, fully renovated 4-bedroom, 3-bath home in the highly sought-after Siesta Isles community... 

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$1,695,000
Provided courtesy of MICHAEL SAUNDERS & COMPANY
47 Photos 5560 Shadow Lawn Drive Sarasota, FL 34242

5560 Shadow Lawn Drive
Sarasota, FL 34242
Siesta Isles
Residential

MLS# A4636955 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2124 Sqft
Area: 34242 - Sarasota/crescent Beach/siesta Key, Subdivision: Siesta Isles

New price! Discover the epitome of coastal living with this stunning waterfront home on Siesta Key, steps from the world-famous white sands of Sies... 

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$1,695,000
Provided courtesy of PREMIER SOTHEBYS INTL REALTY
30 Photos 5502 Shadow Lawn Drive Sarasota, FL 34242

5502 Shadow Lawn Drive
Sarasota, FL 34242
Siesta Isles
Residential

MLS# A4649470 / Active
3 Beds, 4.00 Total Baths, 4 Full Bath, 2337 Sqft
Area: 34242 - Sarasota/crescent Beach/siesta Key, Subdivision: Siesta Isles

Build your Dream Home or renovate the existing home on this Siesta Isles Canal Front lot just a short walk to the cool powdery quartz sands of Sies... 

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$1,389,000
Reduced -$10,000
Provided courtesy of PREFERRED SHORE LLC
50 Photos 5572 Shadow Lawn Drive Sarasota, FL 34242

5572 Shadow Lawn Drive
Sarasota, FL 34242
Siesta Isles
Residential

MLS# A4656346 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2039 Sqft
Area: 34242 - Sarasota/crescent Beach/siesta Key, Subdivision: Siesta Isles

WATERFRONT HOME HALF A MILE TO SIESTA BEACH. Welcome to 5572 Shadow Lawn Drive on Siesta Key. This 3 Bedroom, 2 Bath home sits on a 14,300 SQ. FT. ... 

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$1,100,000
Reduced -$100,000
Provided courtesy of RE/MAX ALLIANCE GROUP
52 Photos 734 Canal Road Sarasota, FL 34242

734 Canal Road
Sarasota, FL 34242
Siesta Isles
Residential

MLS# A4651051 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1412 Sqft
Area: 34242 - Sarasota/crescent Beach/siesta Key, Subdivision: Siesta Isles

Endless possibilities just two blocks from Siesta Beach! Whether you're looking to remodel the structure or build a new island retreat, opportunity... 

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$1,000,000
Provided courtesy of PREMIER SOTHEBYS INTL REALTY
33 Photos 734 Canal Road Sarasota, FL 34242

734 Canal Road
Sarasota, FL 34242
Siesta Isles
Vacant Land

MLS# A4650975 / Active

Endless possibilities just two blocks from Siesta Beach! Whether you're looking to build a new island retreat or remodel the existing structure, op... 

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$1,000,000
Provided courtesy of PREMIER SOTHEBYS INTL REALTY
66 Photos 5353 Shadow Lawn Drive Sarasota, FL 34242

5353 Shadow Lawn Drive
Sarasota, FL 34242
Siesta Isles
Residential

MLS# A4654465 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1596 Sqft
Area: 34242 - Sarasota/crescent Beach/siesta Key, Subdivision: Siesta Isles

With NO WATER DAMAGE OR WATER INTRUSION, you can have peace of mind that you are getting a MOVE IN READY piece of tranquility on the beautiful, wor... 

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$994,000
Reduced -$31,000
Provided courtesy of IRONGATE REALTY INC

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